Cyclocarbopalladation/Cross-Coupling Cascade Reactions in Sulfide Series: Access to Sulfur Heterocycles

Cyclocarbopalladation/cross-coupling cascade reactions were applied for the first time in a sulfur series and represent an efficient route to access sulfur heterocycles. Stille or Suzuki–Miyaura cross-coupling was successfully used as the final reaction. The products are original benzothiolane and i...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 11; pp. 3060 - 3063
Main Authors Castanheiro, Thomas, Donnard, Morgan, Gulea, Mihaela, Suffert, Jean
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.06.2014
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Coordination Complexes - chemistry
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
Sulfides - chemistry
CATALYZED C-S
ARYLATION
EFFICIENT SYNTHESIS
BOND FORMATION
CARBOPALLADATION
ARYL IODIDES
ALKYNES
TETRASUBSTITUTED OLEFINS
SUZUKI-MIYAURA
CYCLIZATION
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Summary:Cyclocarbopalladation/cross-coupling cascade reactions were applied for the first time in a sulfur series and represent an efficient route to access sulfur heterocycles. Stille or Suzuki–Miyaura cross-coupling was successfully used as the final reaction. The products are original benzothiolane and isothiochromane scaffolds with a stereodefined tetrasubstituted exocyclic double bond. To illustrate the application of this method to the synthesis of bioactive molecules, a sulfur analogue of the anticancer agent tamoxifen was prepared as a potential selective estrogen-receptor modulator.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol501165h